Ethanolamine → 2,4-Bis {N-[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]butylamino}-6-(2-hydroxyethyl)amino-s-triazine

HRID 985874Notes

Reaction equation

HRID 985874 reaction equation
[OH:1][C:2]([CH3:49])([CH3:48])[CH2:3][O:4][N:5]1[C:10]([CH3:12])([CH3:11])[CH2:9][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]2[N:23]=[C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]3[CH2:34][C:33]([CH3:36])([CH3:35])[N:32]([O:37][CH2:38][C:39]([CH3:42])([OH:41])[CH3:40])[C:31]([CH3:44])([CH3:43])[CH2:30]3)[N:21]=[C:20](Cl)[N:19]=2)[CH2:7][C:6]1([CH3:47])[CH3:46].[CH2:50]([CH2:52][NH2:53])[OH:51].[OH-].[Na+]>>[OH:1][C:2]([CH3:49])([CH3:48])[CH2:3][O:4][N:5]1[C:10]([CH3:12])([CH3:11])[CH2:9][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]2[N:23]=[C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]3[CH2:34][C:33]([CH3:36])([CH3:35])[N:32]([O:37][CH2:38][C:39]([CH3:42])([OH:41])[CH3:40])[C:31]([CH3:44])([CH3:43])[CH2:30]3)[N:21]=[C:20]([NH:53][CH2:52][CH2:50][OH:51])[N:19]=2)[CH2:7][C:6]1([CH3:47])[CH3:46]

Participants

4

Reactant 3

HCID 700EthanolamineHCID 14798Sodium HydroxideHCID 571517592,4-Bis{N-[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]butylamino}-6-chloro-s-triazine

Product 1

HCID 179307792,4-Bis {N-[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]butylamino}-6-(2-hydroxyethyl)amino-s-triazine

Procedure

The title compound is prepared by the reaction of the intermediate prepared in Example 11 with ethanolamine and sodium hydroxide. The aqueous layer is removed, and the remaining layer is extracted with cyclohexane. Solvent is evaporated at reduced pressure, and the crude product is purified by flash chromatography on silica gel with 1:2 (v/v) hexane/ethyl acetate to afford 4.1 g of the title compound as a white solid, melting at 110-120° C.

Workup

  1. customThe aqueous layer is removed
  2. extractionthe remaining layer is extracted with cyclohexane
  3. customSolvent is evaporated at reduced pressure
  4. customthe crude product is purified by flash chromatography on silica gel with 1:2 (v/v) hexane/ethyl acetate

Sources & evidence

ORD record
ord-ea2b90c0444b459bafee4515cb7621c2
Source dataset
uspto-grants-2005_03
Patent number
US06872832B2

Reaction notes

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